RU2308459C1 - Method for production of 1,3,7,9,13,15,19,21-octaazapentacyclo-[17.5.1.13,21.17,1319,15]octacosane - Google Patents

Abstract

FIELD: organic chemistry.

SUBSTANCE: claimed method includes interaction of 1,3-diaminopropane with paraformaldehyde at room temperature for 10-20 min under stirring and recrystallization of condensation product from ethanol or heptane.

EFFECT: method of high yield.

1 dwg, 2 ex

Description

The invention relates to the field of organic chemistry, and specifically to a method for producing previously known and 1,3,7,9,13,15,19,21-octaazapentacyclo [17.5.1.1 ^3.21 .1 ^7.13 1 ^9.15 ] - octacosan, which has the general structure:

This compound has antiviral, bactericidal and antifungal effects and can be used in medicine and veterinary medicine.

It is known that the condensation of 1,3-diaminopropane with formaldehyde [Die makromolekulare chemie, 1956, v.17, No. 2, p.77] in dimethylformamide leads to the formation of 1,3,7,9,13,15,19,21- octaazapentacyclo [17.5.1.1 ^3.21 .1 ^7.13 1 ^9.15 ] octacosane with a yield (80%).

The technical task of the invention is to increase the yield and simplify the process.

The technical result of the invention is that 1,3,7,9,13,15,19,21-octaazapentacyclo [17.5.1.1 ^3.21 .1 ^7.13 1 ^9.15 ] octacosane is obtained by condensation of 1,3- diaminopropane with paraformaldehyde at room temperature for 10-20 minutes with stirring. A gelatinous mass of white is formed. The reaction mixture was evaporated in vacuo. The residue is recrystallized from ethanol or heptane. Yield 4.2 g (90.1%). The synthesis is carried out according to the following scheme:

Example 1

1,3,7,9,13,15,19,21-octaazapentacyclo [17.5.1.1 ^3.21 .1 ^7.13 1 ^9.15 ] octacosan (drawing)

2.85 g (95.13 mmol) of paraformaldehyde were added to 4 ml (47.56 mmol) of 1,3-diaminopropane with vigorous stirring at room temperature over 10 minutes. A gelatinous mass of white is formed. The reaction mixture was evaporated in vacuo. The residue was recrystallized from ethyl alcohol. Yield 4.2 g (90.1%) 1,3,7,9,13,15,19,21-octaazapentacyclo [17.5.1.1 ^3.21 .1 ^7.13 1 ^9.15 ] octacosane, mp. 165-166 ° C. Found%: C 61.38; H 10.51; N 28.32. C ₂₀ N ₈ H ₄₀ . C 61.18; H 10.27; N, 28.54.

Mass spectrum, m / z (I Rel,%): 393 [M] ⁺ (34), 295 (48), 293 (26), 209 (38), 197 (79), 126 (31), 112 ( 64), 105 (46), 99 (85), 98 (77), 97 (72), 85 (47), 84 (47), 83 (69), 71 (71), 70 (91), 69 ( 87), 68 (75), 59 (49), 58 (90), 57 (73), 56 (100), 55 (64), 54 (57).

¹ H NMR spectrum, δ, ppm: 1.55 br. s. (4Н, 2ССН ₂ С), 2.7 br. s. (8H, 4NCH ₂ C), 3.10 br. s. (8H, 4NCH ₂ N).

Example 2

2.85 g (95.13 mmol) of paraformaldehyde were added to 4 ml (47.56 mmol) of 1,3-diaminopropane with vigorous stirring at room temperature over 20 minutes. A gelatinous mass of white is formed. The reaction mixture was evaporated in vacuo. The residue was recrystallized from heptane. Yield 4.2 g (90.1%) of 1,3,7,9,13,15,19,21-octaazapentacyclo [17.5.1.1 ^3.21 .1 ^7.13 1 ^9.15 ] octacosane.

The identity of the compound is confirmed by a combination of X-ray diffraction (XRD), mass spectrometry, ¹ H-NMR spectroscopy, as well as elemental analysis.

Thus, the proposed method allows to increase the yield of the target product and to simplify the method by reducing the reaction temperature and using solid paraformaldehyde and eliminating the use of a solvent of dimethylformamide.

Claims (1)

The method of obtaining 1,3,7,9,13,15,19,21-octaazapentacyclo- [17.5.1.1 ^3,21 .1 ^7,13 1 ^9,15 ] octacosan, which consists in the interaction of 1,3-diaminopropane with paraformaldehyde at room temperature for 10-20 minutes with stirring, the condensation product is recrystallized from ethanol or heptane.